9,10-二氢-2,7-二硝基-菲 | 69533-68-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 9,10-二氢-2,7-二硝基-菲
• 英文名称: 2,7-dinitro-9,10-dihydrophenanthrene
• 英文别名: 2,7-Dinitro-9-10-dihydrophenanthrene
• CAS: 69533-68-2
• 化学式: C₁₄H₁₀N₂O₄
• 分子量: 270.244
• InChiKey: ITOVIJSDNGFFNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9,10-二氢-2,7-二硝基-菲 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 水 、 tin(ll) chloride 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 溶剂黄146 为溶剂， 反应 3.05h， 生成 菲-2,7-二胺
  参考文献：
  名称：

  Effects of Additional Linkers in Biphenyl-4,4‘-dinitrene on the Low-Lying Singlet−Triplet Energy Gap and Zero-Field Splitting

  摘要：

  Perturbation effects of additional linkers on the spin-spin coupling in biphenyl-4,4'-dinitrene (1) were examined by introducing a linking group between 2- and 2'-positions of 1. Five different doubly linked systems showed triplet ESR spectra corresponding to quinonoid dinitrenes. Curie law analyses suggested that all those tripler states were thermally excited triplet states. In addition, the singlet-tripler energy gaps, which were determined by the Curie law analyses, were well, correlated with their corresponding zero-field-splitting (zfs) D values. The result could be explained by the stability of dinitrene character which is estimated from the resonance energy of the intervening pi-system. Our semiempirical molecular orbital calculations supported the experimental correlation between the singlet-triplet energy gap and the zfs D value.

  DOI：

  10.1021/jp9629710
• 作为产物：
  描述：

  9,10-二氢菲 在 硝酸 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以29%的产率得到9,10-二氢-2,7-二硝基-菲
  参考文献：
  名称：

  Effects of Additional Linkers in Biphenyl-4,4‘-dinitrene on the Low-Lying Singlet−Triplet Energy Gap and Zero-Field Splitting

  摘要：

  Perturbation effects of additional linkers on the spin-spin coupling in biphenyl-4,4'-dinitrene (1) were examined by introducing a linking group between 2- and 2'-positions of 1. Five different doubly linked systems showed triplet ESR spectra corresponding to quinonoid dinitrenes. Curie law analyses suggested that all those tripler states were thermally excited triplet states. In addition, the singlet-tripler energy gaps, which were determined by the Curie law analyses, were well, correlated with their corresponding zero-field-splitting (zfs) D values. The result could be explained by the stability of dinitrene character which is estimated from the resonance energy of the intervening pi-system. Our semiempirical molecular orbital calculations supported the experimental correlation between the singlet-triplet energy gap and the zfs D value.

  DOI：

  10.1021/jp9629710

文献信息

• Molecular structure ofrac-(4R*,4aS*,10aS*)-4-nitro-1,2,3,4,4a,9,10,10a-octahydrophenanthren-4a-ol, an unusual by-product of nitration of a crude 9,10-dihydrophenanthrene
  作者：Franco Fernández、J. López De Lerma、Aurea Perales、Gonzalo Rodríguez

  DOI：10.1007/bf01666094

  日期：1994.7

  AbstractA new nitro-octahydrophenanthrenol has been isolated by nitration of a crude 9,10-dihydrophenanthrene, which was identified by nmr and X-ray diffraction analysis. Crystallographic and molecular structure confirmed the compound as therac-(4R*,4aS*,10aS*)-4-Nitro-1,2,3,4,4a,9,10,10a-octahydrophenanthren-4a-ol. The crystal was triclinic, $$P\bar 1$$ ,a=10.549(3),b=8.530(3),c=7.131(1)Å, α=107.07(3)

  摘要 将粗9,10-二氢菲硝化，分离得到一种新的硝基八氢菲醇，并经核磁共振和X射线衍射分析鉴定。晶体和分子结构证实该化合物为 therac-(4R*,4aS*,10aS*)-4-Nitro-1,2,3,4,4a,9,10,10a-octahydrophenanthren-4a-ol。晶体呈三斜晶系，$$P\bar 1$$ ,a=10.549(3),b=8.530(3),c=7.131(1)Å, α=107.07(3), β=91.62(3), γ=96.27(4)°。环己烷和环己烯环是反式稠合的，分别具有椅式和半椅式构象。这些分子通过羟基氧和两个硝基氧之间的氢桥结合。
• Effects of Additional Linkers in Biphenyl-4,4‘-dinitrene on the Low-Lying Singlet−Triplet Energy Gap and Zero-Field Splitting
  作者：Shigeaki Nimura、Osamu Kikuchi、Tsuguyori Ohana、Akira Yabe、Shigeo Kondo、Masahiro Kaise

  DOI：10.1021/jp9629710

  日期：1997.3.1

  Perturbation effects of additional linkers on the spin-spin coupling in biphenyl-4,4'-dinitrene (1) were examined by introducing a linking group between 2- and 2'-positions of 1. Five different doubly linked systems showed triplet ESR spectra corresponding to quinonoid dinitrenes. Curie law analyses suggested that all those tripler states were thermally excited triplet states. In addition, the singlet-tripler energy gaps, which were determined by the Curie law analyses, were well, correlated with their corresponding zero-field-splitting (zfs) D values. The result could be explained by the stability of dinitrene character which is estimated from the resonance energy of the intervening pi-system. Our semiempirical molecular orbital calculations supported the experimental correlation between the singlet-triplet energy gap and the zfs D value.
• Optical Spectra of Protected Diamine 10-Bond-Bridged Intervalence Radical Cations Related to <i>N</i>,<i>N</i>,<i>N</i>‘<i>N</i>‘-Tetraalkylbenzidine
  作者：Stephen F. Nelsen、Yun Luo、Michael N. Weaver、Jenny V. Lockard、Jeffrey I. Zink

  DOI：10.1021/jo060466l

  日期：2006.5.1

  The optical absorption spectra of the delocalized intervalence radical cations of seven o,o'-linked benzidine derivatives that have the nitrogens protected as 9-(9-aza-bicyclo[3.3.1]nonan-3-one) derivatives are discussed and compared with that of the p-phenylene radical cation. The linking units are CH2, CH2CH2, NMe, S, SO2, and C=O, and we also studied H, H ( the unlinked benzidine). The lowest-energy absorption band is assigned as the transition from the antibonding combination of symmetrical N and aromatic orbitals to the antibonding combination of the antisymmetric N and aromatic orbitals using TD-DFT calculations, and a good correlation between the observed transition energies and those calculated using the simple Koopmans theorem-based "neutral in-cation geometry" calculations on the UB3LYP/6-31G* structures is found. The use of the two-state model that equates the electronic interaction through the bridge between the amino groups with half of the lowest transition energy is seriously incorrect for these and other delocalized intervalence compounds. The problem of extracting the electronic interactions that actually are involved from calculated transition energies is discussed.
• Nitration of a Crude 9,10-Dihydrophenanthrene
  作者：Ana Eir�n、Franco Fern�ndez、Generosa G�mez、Carmen L�pez、Ana Santos、Gonzalo Rodr�guez

  DOI：10.1002/prac.19943360112

  日期：——
• Yadav, Ram Naresh; Banik, Indrani; Banik, Bimal Krishna, Journal of the Indian Chemical Society, 2018, vol. 95, # 11, p. 1377 - 1380
  作者：Yadav, Ram Naresh、Banik, Indrani、Banik, Bimal Krishna

  DOI：——

  日期：——